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4 protocols using 2 methoxy 1 4 naphthoquinone

1

Authentic Standards for Carinostoma Secretion Analysis

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Authentic standards of n-alkanes (C7–C36), acetophenone, octan-3-one, 5-methyl-heptan-3-one, 6-methyl-5-hepten-2-one, 1,4-naphthoquinone and 2-methoxy-1,4-naphthoquinone for a comparison of gas chromatographic–mass spectrometric data to components found in the Carinostoma-secretion were purchased from Sigma (Vienna, Austria). 6-Methyl-1,4-naphthoquinone was prepared according to Bruce and Thomson (1952 (link)); as oxidizing reagent we used CAN (=cerium IV ammonium nitrate from Sigma, Austria). For two further compounds, namely 2-methoxy-6-methyl-1,4-naphthoquinone and 4-chloro-1,2-naphthoquinone, we used known natural sources for reference, namely the secretions of P. quadripunctatum (Raspotnig et al. 2010 (link)) and Cyphophthalmus (formerly Siro) duricorius (Raspotnig et al. 2005 (link)). O-Methyl oximes of ketones in the Carinostoma-extracts were prepared by adding 200 μl of methoxamine (MOX) reagent (=2 % methoxyamine-hydrogen chloride in pyridine, Thermo Scientific, Vienna, Austria) to 60 μl of ketone-rich extracts in hexane, followed by incubation at 70° for 1 h. The products were washed twice with water, dissolved in 60 μl of hexane, and an aliquot (1.5 μl) was directly used for GC–MS.
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2

Synthesis of Substituted Naphthoquinones

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6-Methyl-1,4-naphthoquinone was prepared based on a procedure described by Bruce and Thomson (1952) (link). As oxidizing reagent we used CAN (cerium IV ammonium nitrate). 4-Chloro-1,2-naphthoquinone was synthesized from 2,4-dichloro-1-naphthol in benzene using lead(IV)acetate as oxidizing reagent as recently described (Raspotnig et al., 2005 (link)). An alkane standard (a mix of C9-C36 n-alkanes), all reagents as well as authentic references for 1,4-benzoquinone, 1,4-naphthoquinone, 1,4-naphthalenediol, 2-methoxy-1,4-naphthoquinone, 2-methyl-9,10-anthraquinone, 1,2-dimethyl-9,10-anthraquinone, 1,4-dimethyl-9,10-anthraquinone, and 2,3-dimethyl-9,10-anthraquinone were purchased from Sigma-Aldrich (Austria).
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Naphthoquinones and Analogs Acquisition

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Naphthoquinones and their analogs (Fig. 2) were purchased from the following companies: juglone (97%), lapachol (97%), 2,3- dichloro-1,4-naphthoquinone (98%), vitamin K1 (98%), and naphthazarin (98%) were purchased from Aladdin Industrial Co. Ltd. (Shanghai, China); plumbagin (97%) was purchased from J&K Scientific Ltd. (Beijing, China); menadione (98%), 1,4-naphthoquinone (99%), shikonin (97%) and lawsone (98%) were purchased from Meryer Chemical Technology Co. Ltd. (Shanghai, China); 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (97%) was purchased from Tokyo Chemical Industry Co. Ltd. (Tokyo, Japan); 2-methoxy-1,4-naphthoquinone (98%), 2,3-dibromo-1,4-naphthoquinone (97%), acetylthiocholine iodine, 5,5′-dithiobis(2-nitrobenzoic acid), L-reduced glutathione and 1-chloro-2,4-dinitrobenzene were purchased from Sigma-Aldrich Co. Ltd. (St. Louis, USA) and from Toronto Research Chemical Inc. (Toronto, Canada); and alkannin (98%) and ivermectin (94%) were purchased from Shanghai Yuanye Biotechnology. Co. Ltd. (Shanghai, China).
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4

Synthesis of Substituted Naphthoquinones

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6-Methyl-1,4-naphthoquinone was prepared based on a procedure described by Bruce and Thomson (1952) (link). As oxidizing reagent we used CAN (cerium IV ammonium nitrate). 4-Chloro-1,2-naphthoquinone was synthesized from 2,4-dichloro-1-naphthol in benzene using lead(IV)acetate as oxidizing reagent as recently described (Raspotnig et al., 2005 (link)). An alkane standard (a mix of C9-C36 n-alkanes), all reagents as well as authentic references for 1,4-benzoquinone, 1,4-naphthoquinone, 1,4-naphthalenediol, 2-methoxy-1,4-naphthoquinone, 2-methyl-9,10-anthraquinone, 1,2-dimethyl-9,10-anthraquinone, 1,4-dimethyl-9,10-anthraquinone, and 2,3-dimethyl-9,10-anthraquinone were purchased from Sigma-Aldrich (Austria).
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